


Brother Let Me Be Your Shelter..Be The One To Light The Way..Bring You Home..

by Shtwriter_yup_datsme



Series: Leo Webb/Dean Winchester [4]
Category: Supernatural
Genre: Bad Parent John Winchester, Bisexual Disaster Dean Winchester, Drinking & Talking, Friendship/Love, Love Confessions, M/M, Past Relationship(s), Smut
Language: English
Status: Completed
Published: 2020-06-05
Updated: 2020-06-05
Packaged: 2021-03-03 19:48:39
Rating: Not Rated
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 2,588
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/24561091
Author URL: https://archiveofourown.org/users/Shtwriter_yup_datsme/pseuds/Shtwriter_yup_datsme
Relationships: Castiel/Dean Winchester, Leo Webb/Dean Winchester
Series: Leo Webb/Dean Winchester [4]
Series URL: https://archiveofourown.org/series/1775263
Kudos: 12





	Brother Let Me Be Your Shelter..Be The One To Light The Way..Bring You Home..

Dean knocked on Cas' bedroom door, it was open so Dean stared at him just watching Cas sit there thinking "Hey Cas.." He finally said, clearing his throat

The angel perked up immediately "Dean-where have you been?- Sam almost died-" The angel started rushing his words, Dean put a hand up "I know- I know..Eileen filled me in" He said "But Sam's okay right?"

Cas sighed nodding "For now he is stable yes"

"Good," Dean looked Cas over "..There's something else I wanted to talk to you about"

"What is it?" He didn't really think they were on too good terms, Dean stepped into the room and shut the door behind him he sat down with Cas and just started talking- laying everything down on the table

He started with his feelings and repression, Cas listened intensely- he didn't even say anything when Dean said he was in love with him but decided to keep it a secret 

There were so many emotions in the air, even Cas confessed his feelings of love to Dean as well- Dean was slightly surprised to say the least

At some point they started to kiss, the first one was slow but turned heated fast, clothes were flying everywhere and moans were muffled by the sheets, soon enough the room smelled of sex and no longer sexual tension

It was late into the night, Dean layed still on his bed arm slung behind his head on the pillow, he tried to slow his breathing as to not wake the angel sleeping peacefully on his bare chest

He looked down at Cas' sleeping state and he kissed the man on the forehead before very carefully slipping out of bed

Cas sputtered but he didn't wake- Dean grabbed his hotdog pants and robe stealing one quick glance at Cas before leaving

He walked all the way to the kitchen, he grabbed a glass and some whiskey, he sat down and began to drink not a lot, not caring to notice Sam was already sitting in the kitchen

"Dean?- what are you doing up?" He asked and his brother shrugged "..I could ask you the same question"

Sam eyed the bottle of whiskey but didn't say anything about it, to his surprise it was Dean who spoke "Hey Sam?-..can I tell you a story?" He asked his brother as he sloshed his drink back and forth in his glass

Sam took a moment to answer "Um..yeah okay"

Dean gave it a few seconds before he started "..My first kiss with a.. _boy-_ I was 14, I didn't even know what I was doing- I was supposed to be into girls and I was..but I knew that I had liked it..kissing him" He sighed "I was 15 when I started to do other stuff with guys and 16 when dad found out.."

"He asked me if I was _gay_..and I told him I wasn't..I still liked girls but I liked guys the same"

"..How'd he take that?" Sam asked quietly "Well despite everything he'd done to me he tried to understand it but I could tell..it wasn't the same"

"He'd treat me different.. like I wasn't even his kid anymore" Dean sighed "His approval mean't everything to me so I buried my feelings, and every girl he saw me with I started to become his son again"

"..You were at Stanford when I met this guy, Leo- he joined me and dad hunting and we started having sex.. and along the way we became great friends..Lee even helped me understand who I was- y'know?- help me accept it"

Sam shook his head he couldn't stay silent anymore "But you've never said anything..Dean are you ashamed?"

Dean shook his head softly "No..not anymore"

Sam eyed his brother carefully "Leo? were you in love with him?"

Dean pondered for a moment "Yeah I think- I _knew_ I was" He corrected "But I never told him- my first mistake obviously " He admitted easily, not overthinking how calm Sam was "..But after him I was too scared..I mostly went for girls- didn't want to act on my _'gay urges'_ as dad once called it"

"Hell, I was even scared of what _you_ would think of me- last thing I needed was my little brother hating me for feelings I didn't even ask for"

Sam wanted badly to tell Dean how he would never judge him but he let his brother continue

"But then I met Cas and it was like all of the feelings I had repressed just came back and it was nice..to have _someone_ \- even if it wasn't physically or romantically, we were friends- and I was okay with that..it was until purgatory Benny helped me realise that I was head over heels for the guy"

"It freaked me out so much I didn't even want to think about it so I kept it in- just like everything else I buried that part of me for over a decade.."

"So why are you telling me now?" Sam asked gently and Dean took a moment "This case..I met Leo again and I fell back into an old habit" Dean said "He even knocked some sense into me- told me I was being a complete idiot.."

~

When Dean had seen Leo again it was..surprising to say the least, it was weird how easily he felt back into old habits with his old flame

It was easy

Dean was feeling pretty horrible before he saw Leo in the crowd of people but afterwards he was like a different person..smiling, laughing, reminiscing..

He accepted Leo's offer to stay at his place for a night after they had finished the case, he didn't really know if it was a good idea but screw his brain- he made bad decisions all the time

Just as he was saying goodnight to Dean Leo abruptly kissed him like he had wanted to do all night, thinking the man would pull away fast and ask him what the fuck he was doing but it never came

Dean was a little shocked as Leo swallowed the surprised hum that came from him and though he was hesitant at first, his hands wrapped around Leo's neck, he pulled at Lee's lip gently with his teeth as they separated "Lee.." He breathed and _god_ did that do things to Leo- Dean's voice was rough and sexy and hearing his name said like that just fed his erection "I was hoping you'd do that" Dean whispered; he couldn't tell if it was him or the alcohol talking- probably both

They smiled against each others lips and made their way to the bed, Leo pulled off Dean's flannel and lifted up his shirt and Dean did the same to his, they fell onto the bed and Dean was on top pinning Leo to the bed

He unbuttoned Leo's jeans and yanked them off, he stared up at Leo as he teased the waistband of his boxers, Leo bucked up into Dean's hands "Don't tease Winchester"

"You gonna make me _Webb_?"

"Do you want me to?"

Dean shrugged teasingly and took Leo's boxers off, he used to be experienced but after years of sexual repression he may have been a little rusty so he didn't complain when Leo decided he wanted to be on top flipping Dean over

He stripped Dean down to his nakedness and grabbed some lube and a condom from his nightstand pushing Dean's legs up, he slipped a lubed finger into Dean patiently stretching him out, he waited a little before adding a second finger, Dean rolled his eyes "Fuck Lee I'm ready"

Leo grinned "God I can't believe I forgot how needy you are" Dean scoffed "I am not _needy_ just because I don't want to wait forever to be stretched out- I've had worse happen to my body"

Leo hummed obviously unconvinced and Dean laughed, "Just come up here and kiss me you asshole" He muttered and Leo happily complied sliding back up Dean's body to plant a soft kiss on his lips "Missed you" Leo whispered against Dean's lips

Dean kissed him back "..Me too" He said honestly even though they both knew that this was a one time thing, "You sure you wanna do this?" He asked quietly

Leo smiled "100 percent" He reached down to take his cock and he pressed it against Dean's hole, Dean groaned eyes leaving Leo's as he was penetrated

It'd been so long he felt new to the feeling, but Leo made sure he started gentle "Dean..still so tight as ever" Leo moaned into his neck making Dean shiver, he chewed his lip "You complaining?"

Leo grinned gripping Dean's waist and giving an extra hard thrust to make Dean yelp "Fuck!" _Well.. a_ _s g_ _entle as_ _he_ _can be_

"You know I'd never" He kissed Dean again and the man under him wrapped his arms around his neck, to kiss him- grinding his hips down with every thrust Leo gave

He missed this, sex with Leo- it made him feel 22 again- like him and Leo were back in time, messing around behind his father's back and he wasn't even thinking about Cas, _that's_ how bad he needed this- he _wanted_ this, Dean whimpered clenching around Leo's cock as he wrapped his legs around his back "Lee..harder" He groaned and Leo kissed again him working his hips faster and harder with each thrust

His body reacted and he clamped down around Leo's cock "Lee I'm gonna cum" With a few deep thrusts from Lee he was creaming all over his chest while the condom was filled to the brim with cum

After a few seconds Leo pulled out of Dean's well fucked hole and fell beside him on a pillow both men panting breathlessly

~

The next morning they had breakfast together and Dean told Leo some more about Sam, there wasn't any romantic or sexual tension they just hung out until Dean needed to leave

Dean was stood by the impala just outside of the bar saying his goodbyes to Leo, the scene was strikingly similar to the last time they had parted but neither was gonna mention it

Leo looked Dean over "Y'know this whole time you never once mentioned that you were interested in someone"

"What?- where'd you get that idea?'

Leo scoffed "Come on _I know you_ Dean" He smiled "What's her name?- or _his?-_ if you ever took my advice"

Dean sighed Leo could always see right through him " _His_ name is Castiel- _Cas-_ he's an angel"

"Like an _actual_ angel?"

Dean nodded shortly "Yup- I've got no chance right?" Leo frowned, not fully convinced "Not necessarily- what's the story behind that one?"

"..He pulled me out of hell"

Leo's eyebrows rose "Damn- I definitely can't compete with that" Dean rolled his eyes though flustered "Shut up" He muttered playfully, "..Dean you love this guy don't you?"

"Yeah I do Lee"

"Then _tell him-_ don't let history repeat itself tell him how you feel before it's too late- you and him don't have to be us" Leo said sincerely, and with a heavy heart

Dean furrowed his brows "..Are you saying that if I'd just told you how I felt earlier..we'd..we'd be together _right now?_ " He'd never really thought about it like that..if he'd just been less of a coward..things could have been so much different

Leo gave his old friend a sad smile, he leaned in and kissed Dean on the lips, Dean barley got a chance to kiss back before Leo had pulled away "Goodbye Winchester" And just like that he walked off leaving Dean _hella_ confused

He got into his car and started up the engine shaking his head and remembering just how cryptic and annoying Leo Webb could be, he looked at the bar one last time "Yeah..I love you too asshole"

~

Sam was in shock but was doing his best to hide it "Dean you hid that from me?" He questioned "A whole other life with someone you _obviously_ care about?"

Dean downed the rest of his whiskey "-Sam you know how closed off I am- at least I'm telling you now- rather than not at all"

"..What about Cas?- are you gonna tell _him?_ "

Dean hesitated a little "I already did..he's _sleeping it off_ in his room" Sam's eyebrows shot up "You guys had sex?- did you tell him about Leo?" -more importantly that you had sex with him?- but Sam didn't say that part

Dean nodded, "All cards on the table" He explained "I didn't mean for it to go that way but..I guess opening up can do that" Dean looked at Sam "So what's your take on..my.. _everything?_ "

"Well thanks for finally telling me..I mean I guess I kind of already knew"

Dean's eyebrows shot up fast "What?- you knew?- and you didn't say anything?"

"I figured it out when I was 13 you kept blowing off that girl from school- I thought you were just being a -hard to get- ass but then I saw how you looked at her _brother_..I put two and two together fast" Sam explained nonchulantly "I didn't say anything because I figured you'd tell me when you were ready- didn't think it take over 2 decades"

Dean pursed his lips; that sounded fair "And what about Cas?"

"If you guys are actually gonna try then I'm happy for both of you-..you deserve it"

"Thanks..Sammy- you have know idea how much that means to me"

Sam shrugged "I have hangups too Dean"

Dean recoiled "Like what?- you take every chance you get to spill your feelings"

Sam paused and he took a deep breath "..Gabriel" was all he said and Dean blinked, he didn't say anything but the look on Sam's face said it all and Dean understood he knew the archangel and Sam were close but how close was Sammy's secret, his brother sighed "Couple that with..feelings that were never resolved and a kiss that meant everything to me.."

He cleared his throat "..You gonna finish that?" Sam asked referring to the bottle of whiskey, Dean shook his head "Nah..Cas doesn't like me drinking so much- I'm trying to cut back"

Sam smiled at how Dean loved Cas enough to change for him "Well sleep it is then- goodnight" Sam sighed and stood heading out to his bedroom

~

"Where'd you go?" Cas asked when Dean got back to the room, he had recently woken up and was waiting patiently for Dean

"I needed a drink"

Cas visibly deflated "Dean.." His partner sighed "I know I know- you don't like my _excessive_ drinking, I'll try and calm it down" He smiled climbing back into bed with Cas giving a kiss to his cheek "Promise"

Cas flushed softly, "Y'know I wasn't just drinking, I also talked to Sam" Cas sat up and flipped on the lamp, "What about?"

"Pretty much what I told you" Dean got back into bed "..You actually told him?" Cas sounded surprised

Dean nodded "Yeah I did Cas.." He sighed "I've had forever staring me in the face for too long and I don't want to hide that"

Cas smiled at him, soft and beautiful-and weirdly in that moment for the first time in weeks Dean truly felt like everything was going to be okay.


End file.
